


The Bet

by hunter_king



Series: Supernatural - Wincest [46]
Category: Supernatural
Genre: Barebacking, Bottom Sam Winchester, M/M, Slash, Swearing, Top Dean Winchester
Language: English
Status: Completed
Published: 2019-11-24
Updated: 2019-11-24
Packaged: 2021-02-26 04:54:53
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,766
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21547942
Author URL: https://archiveofourown.org/users/hunter_king/pseuds/hunter_king
Summary: Sam makes the mistake of betting Dean that he’s the better poker player. Dean agrees to the bet, with one stipulation; the winner gets to name whatever he wants and the loser can’t refuse. Sam loses and discovers that what Dean wants as his prize is him - in every way.
Relationships: Dean Winchester/Sam Winchester
Series: Supernatural - Wincest [46]
Series URL: https://archiveofourown.org/series/1190095
Comments: 2
Kudos: 155





	The Bet

**Author's Note:**

> Written for the SMPC challenge  
> Beta'd by jdl71  
> Prompt given to me by the lovely jdl71

Sam wasn't sure why he thought this had been a good idea. They were just between hunts right now, and he could tell that his brother was getting antsy, so Sam was trying everything he could think of to make Dean feel better. After all, Dean had been acting strangely since their father had gone and made that demon deal with old yellow eyes. At least that's what Dean had convinced himself, anyway. And if there was one thing he knew about Dean Winchester, it was that he couldn't turn down a bet where a poker game was involved.

So now, Sam was sitting opposite of Dean at the small table in their dingy motel room with a shitty hand, and one terrible poker face. Sam _really_ didn't know why he thought this had been a good idea. And to add to it, Dean's one stipulation to playing the game had been the winner gets to name whatever he wants, and the loser couldn't refuse. Now, Sam was running through scenarios in his head about what Dean could possibly want – none of the outcomes were that great, either.

Taking a chance, Sam glanced at his brother, trying to gauge whether or not Dean had a good hand. Honestly, his brother had one of the best poker faces around, so Sam had no damn idea what cards were between Dean's fingers. Grabbing a two of spades and a four of hearts, Sam tossed them into the middle of the table. “Gimme two,” he muttered, scooping up his new cards when Dean flicked them in his direction.

Of course, the cards he was dealt were both no help to his current situation. He had an ace-high, so Sam knew that he was going to lose. Briefly, Sam wondered if Dean had set the deck, though he quickly shoved that thought away. Dean had allowed Sam to shuffle so he _knew_ he wasn't cheating. Not that Sam thought Dean would cheat in a game of poker. Sam was just a sore loser – he was completely fine admitting that to himself.

“What do you got, Sammy?” Dean asked, smirking at the younger man from across the table. His hand wasn't all that great, but he had a feeling it was better than his brother's. After all, Sam's poker face was shit, and Dean knew if Sam had anything worth getting excited about, he wouldn't have been able to hold it in. 

Reluctantly, Sam flipped his cards over, showing Dean his hand. “Ace-high,” Sam answered, frowning deeply at the cards he'd placed on the table. He knew there was no way in hell Dean was going to be able to lose to this hand. He also knew that he was pouting a bit, but he couldn't bring himself to care enough to stop.

A wide smile came to Dean's lips when Sam revealed his cards, the older man knowing for sure he had it in the bag now. Slowly, Dean spread his cards on the table for Sam to see. “Pair of threes, Sammy,” Dean smirked, grabbing his beer and taking a long pull. “Looks like I win.”

When Dean gloated, Sam barely resisted the urge to roll his eyes. “Alright, yeah, you win,” Sam grumped, grabbing his own beer bottle and finishing it off. “Go ahead, Dean. Name your prize. Are you gonna make me...clean the Impala for a week straight? Or...make me go on food runs for a while?”

While all of those things Sam was offering right now seemed like they'd be awesome, Dean had other plans. Being with Sam every day for the past year had done things to Dean – made old feelings creep back up to the surface, and it was starting to bubble over. And Sam felt it, too – Dean knew he did. When their father had been taken from them, Sam had allowed Dean to take comfort in him. Much like last year when Dean allowed Sam to share his bed so the nightmares about Jessica would stop. Nothing major had happened, just some kissing and light touching. But it made Dean want more. And if Sam hadn't been into it, he would have stopped Dean.

Slowly, Dean leaned across the table, licking his suddenly too dry lips. “That all sounds pretty good, Sammy,” Dean assured the younger man with a nod. “But I had something else in mind.” His eyes locked with Sam's, heat shooting through his body at the thought of having his little brother all to himself. 

Ever since that hunt a few weeks ago, Dean had been barely able to keep his hands to himself. Sam had been pouting and brooding because Dean had been _flirting_ with Jo, and it had been one of the hottest things Dean had ever seen. His hand reached out, finger brushing along the back of Sam's knuckles, just tucking up the gap Sam's cast left. “I want you, Sammy.”

For a second, Sam thought that Dean was messing with him. It would just be like Dean Winchester to pull a prank so colossal that it rivaled all of their other prank wars. But Sam wasn't sure. On the one hand, he could say something and make Dean think he wasn't into it, which would have been a lie. But on the other hand, if Dean was messing with him right now, Sam wasn't sure he could stay here tonight. He'd need time to cool off. So, Sam just stayed silent, eyes ticking from Dean's finger tracing over his knuckles to his brother's face.

The lack of response from Sam had the usually confident older Winchester feeling very unsure of himself. “Look, I know I said you couldn't refuse,” Dean started, catching Sam's eyes once more and holding them, “but you don't have to do anything you don't want to. I can pick something else. I'm not gonna make you do anything.”

Sam knew that his brother wasn't going to make him do anything. Dean was the one person Sam trusted on this Earth. So, he was going to go for it. If Dean was just messing with him, Sam would leave for the night to cool off – that made perfect sense. “N-No,” Sam answered, shaking his head as he dragged his tongue along his lips. “I mean...the deal was that the loser doesn't get to refuse, right?” Shrugging, Sam continued, “I mean...you won. Fair and square. You should...get your prize.”

A small smile came to Dean's lips when Sam spoke. “Good,” he grinned, pushing himself from his chair. “C'mere, Sammy,” Dean instructed, arms wrapping around Sam's waist and tugging him impossibly closer once he could reach. His hands shoved up Sam's T-shirt, fingers laying flat against Sam's smooth flesh. “God, Sammy...kiss me.”

Without hesitation, Sam surged forward, crushing his lips against Dean's. It was desperate, much like the way it always was when they let themselves cross this line. Dean was kissing him back, so Sam figured that he wasn't messing with him. Convinced that this really was Dean's prize, Sam let go, giving his brother everything he had. After all, he'd been waiting for this for a very long time. Those little snippets of Dean taking comfort and giving comfort just weren't enough. Sam needed more.

When Sam kissed him, Dean nearly fell backwards from the force. Steadying them, Dean crowded into Sam's space, pressing the younger man back against the table they'd been playing poker on. If he wasn't so worried that the table wouldn't hold under their weight, Dean would have just shoved Sam onto the tabletop and taken him right there. But he couldn't run the risk of Sam getting hurt if those table legs snapped. 

Only when they both needed air did the kiss break, Dean pressing his forehead against Sam's so that he didn't lose the contact. Dean's fingers worked quickly to get Sam out of his over shirt, tossing the flannel into the corner once it was out of his way. He then gripped the hem of Sam's shirt, yanking it over the younger man's head before he crushed their lips together once more. As the kiss continued, Dean turned them so that he could walk Sam toward the bed, pushing his little brother onto the mattress once he was close enough.

As soon as Sam was on the bed, Dean dropped to his knees in front of him. His hands moved to the fastenings of Sam's jeans, popping them open with skilled fingers. In his haste to get Sam out of the remaining clothing he was wearing, Dean's short fingernails scratched at Sam's hips, leaving little red marks in their wake. 

Now that Sam was completely naked, he felt vulnerable and exposed. Quickly, he reached for Dean, hands grasping at his brother's black T-shirt and tugging at it. “Get this off,” Sam complained, his bottom lip protruding outward in a pout when he couldn't get the clothing to budge.

Chuckling, Dean reached behind himself and gripped the collar of his T-shirt before he tugged it off of his torso. Immediately, Sam's hands were on his freshly exposed skin, the younger man touching every inch he could reach. Sam seemed almost mesmerized by Dean as his hands slid over his bare chest. Again, Dean surged forward, crushing his lips against his brother's once more. 

“Tell me you want this too, Sammy,” Dean ordered when the kiss broke, moss green eyes searching Sam's face for any signs of hesitation. Sam made the comment that it was only fair that Dean got his prize, and he hadn't made any moves to stop him so far, but Dean wasn't about to force his brother into this. “I need to hear you say the words.”

Sam had to fight the urge to laugh when Dean ordered him to speak. Sam wouldn't have been doing this if he didn't want to. He would have said no and left the motel room. “I want this,” Sam assured his brother, fingers moving to work open Dean's jeans. “I want _you_.” As soon as Sam had Dean's jeans open, he tugged both Dean's jeans and boxers off his hips, licking his lips in anticipation when his brother's hard cock sprang free.

Before Dean had a chance to start a conversation with him again, Sam leaned forward, lips wrapping around the head of his brother's leaking cock. Sam's champagne hazel eyes peered up at Dean from under his long bangs as Sam took more of his brother's cock into his mouth, moaning softly around Dean's flesh. His hand wrapped around the base of Dean's member, strong fingers stroking the lower half of Dean's cock that wasn't in his mouth.

When Sam took his cock into his mouth, Dean's knees almost buckled in his surprise. “Ungh...Sammy,” Dean groaned, one hand slapping against Sam's shoulder to keep him grounded while the other buried itself in Sam's chestnut locks. “Fuck...Sammy, don't stop.” Slowly, Dean's eyes slipped closed, head falling back as he gently rocked his hips into Sam's mouth. He knew he couldn't let this go on long – he didn't plan on blowing his load in Sam's mouth tonight.

After a few moments, just as Dean felt himself trying to let go completely, he pushed at Sam's shoulder. “Sammy, stop,” Dean grumbled, biting into his bottom lip. “Don't wanna cum, Sammy. Not yet.” Relief flooded through him when Sam actually listened and pulled off. “Lie back,” Dean instructed, crawling onto the bed with Sam as he reached for the top drawer of the nightstand. He'd checked it last night – there was a bottle of unopened lube there. All of these skeevey motels came equipped with it.

Lube in hand, Dean settled between Sam's legs, nipping at the younger man's bottom lip. “Mmmm...Sammy,” he breathed, popping the cap on the lube with his thumb. “I wanna be inside you so bad. You have no idea.”

Again, Sam had to fight the urge to chuckle when Dean told him he had no idea. Sam had a pretty damn good idea because he was sure he was feeling it, too. “I know,” Sam argued, nodding erratically. “Please...I need you. Please, Dean?”

“Shhhh...Sammy, m'gonna take care of you,” Dean promised, nodding as an extra assurance. When Dean's finger breached him, Sam moaned softly, back arching off the bed. “Fuck,” he groaned, head falling to the side on the pillow. Dean added a second before Sam really had time to adjust to the first, causing Sam to hiss in a mixture of pain and pleasure. “Dean...” he breathed, one hand moving to grip his brother's shoulder.

When Sam said his name, Dean allowed his eyes to dart up to look at his brother. Sam looked like he was enjoying what Dean was doing, so he wasn't about to stop. “Shhh Sammy, s'okay,” Dean whispered. His head dipped to suck at Sam's exposed pulse point, adding a third finger when he felt Sam was prepared for it.

There was a war waging inside Sam's head right now. On the one hand, he wanted Dean so badly, he could almost do without the preparation making him wait even longer. But on the other hand, he knew he'd regret it if Dean didn't actually take his time with him. And honestly, Sam knew Dean would never run the risk of not preparing him enough. Dean would never hurt him like that. It was a little uncomfortable, but Sam knew that feeling would pass. It always hurt a little bit when he would push his fingers into his body at first, too. And Dean's fingers were thicker than Sam's, so he'd known it would sting a bit going in. 

He was dragged out of his thoughts when Dean pulled his fingers away. “Are you ready, Sammy?” Dean breathed into his ear. And this was it. This was _finally_ happening. He could feel his heart hammering against his chest like it was about to beat right out of him. Sam's eyes ticked down to Dean's crotch, watching his brother's hand glide over his hard shaft as Dean lubricated himself. His tongue darted out to wet his lips on its own accord as Sam nodded. 

The few times that Sam had fingered himself during masturbation couldn't have prepared him for the pain that having sex with another man actually entailed. He thought that three fingers would have been enough to open him up for Dean’s cock, but he’d been wrong. His hands gripped at Dean’s shoulders, fingernails digging into the soft skin there as he breathed through the pain.

It was slow going, Dean stopping every few inches to make sure Sam was all right. He stopped once he was fully sheathed inside Sam, his arms shaking with the effort of keeping himself from moving. Dean could see the pain on Sam’s face and he noticed that Sam’s erection had dwindled marginally, and he was wondering if this had been such a good idea. But they were too far to quit now. Sam would be fine after a few minutes – his body would adjust and they could continue where they left off. 

Sure enough, after a few moments, Sam wiggled experimentally, breathing in a shocked gasp at the pleasure he felt now that he was used to the invasion. “Ungh…D-Dean, you can move now,” Sam explained, one hand moving to fist in Dean’s hair as he yanked him down into a heated kiss. 

Dean didn’t need to be told twice. He kept his movements slow and gentle as he pulled almost all of the way out of Sam, sliding back in slowly, watching Sam’s reaction to his movements. Satisfied that Sam seemed to be enjoying himself, Dean repeated the action, moving just a bit faster – a little harder – this time. Again, Sam seemed to be fine with it, so Dean kept going until he was all but slamming his cock into Sam. 

And it felt good. It felt so fucking good. Sam was tight and he was gripping Dean’s cock just right on every thrust. Angling his hips, Dean smirked slightly when Sam gasped and then groaned in pleasure. The pure pleasure on Sam’s face let Dean know that he’d hit Sam’s sweet spot. So he did it again. And then again, one hand fisting in the sheets beneath Sam while the other fisted in Sam’s hair when Sam’s inner muscles clamped down on his dick just right. “Fuck, Sam,” he breathed, head dipping to nip and suck at Sam’s neck and shoulder.

Although his erection had dwindled down when Dean first pushed into him, Sam was fully erect once more, pre-cum leaking from the tip of his penis. He knew he wasn’t going to last much longer. Dean hadn’t even touched his dick and Sam was going to blow his load. 

He needed something – _anything_ to make this last longer. He wasn't ready for this be over just yet. Quickly, Sam shoved Dean off him, crawling on top of the older Winchester and pinning him to the bed. “I wanna be on top,” he whispered softly when Dean looked up at him in confusion.

Once he had Dean underneath him, Sam leaned down, crushing his lips to Dean’s, tongue pressing against the seam of his lips and demanding entrance, which he was soon granted. He pulled back soon after, pushing up off Dean’s chest and turning at the waist, hand gripping the base of his brother's shaft before slowly lowering himself down onto him. Soft moans and groans broke from Sam’s throat as he sheathed Dean inside himself, not stopping until Dean was buried to the hilt. Once he had Dean all the way inside him, both of his hands came down to rest against Dean’s chest as his head fell forward, hair flopping down to cover his face.

It felt so good to be with Sam like this, which kind of surprised him since he wasn’t one to ever give up control. But, as with most things in his life since he’d realized his feelings for his brother went deeper than he could possibly imagine, there was something about Sam that just made Dean give in to his every request. Probably because he knew that it would be good as long as Sam was in the equation.

When Sam had him buried to the hilt, Dean moaned as his head pressed back against the bed once more, watching his brother from beneath hooded eyes. God, if he thought Sam was hot before, seeing him with his hair all in his face just made him so much hotter; it was taking all Dean had not to thrust up into Sam before the younger man was ready. If he moved now, Sam would fall off because he wasn't steady enough. And that wouldn't have been a picnic for either one of them.

Feeling Dean’s hands on him, Sam opened his eyes to mere passion-glazed slits. Turning his head slightly to the side, Sam pressed his lips against Dean's palm, his teeth lightly scraping over the skin there as he laced their fingers together on his cheek. Slowly, he gave an experimental thrust backwards, moaning when Dean’s cock hit his prostate. He was definitely ready now.

Sam pressed down against Dean’s chest, making sure not to fall off Dean in this unfamiliar position as he used his knees to push off the bed, raising himself almost completely off Dean’s dick before he slid back down.

Moans and groans filled the room as Sam continued to ride Dean. There was no way he was going to last much longer, having been achingly hard since Dean started touching him. And he was setting the pace just right, for both of them if Dean’s moaning was any indication, and Dean’s cock was hitting his prostate with every thrust. No, Sam was _definitely_ not going to last much longer at this rate. “D-Dean,” he gasped, fingers curling around his brother's nipples, short blunt nails digging into the flesh. “I’m close.”

The way Sam’s inner muscles were clenching around his achingly hard flesh let Dean know it wasn’t going to be long before he was cumming inside his brother. His hands on Sam’s hips tightened their grip a little as he moaned in pleasure, his head once again pressing into the back of the mattress. “Yeah, me too Sammy,” he assured Sam, nodding slightly. “Do it. Cum for me, Sam.” One hand moved to grip the base of Sam’s shaft and began to slide along his brother's length, using the pre-cum oozing from Sam’s slit to help slick the way.

Once Dean told him to cum and his hand soon followed, Sam was gone. There was nothing he could have done to stop himself from cumming at that moment, even if he knew it would have caused the world to end. His back arched, body tensing and his nipples pebbling as he felt heat pool low in his belly, balls drawing up close to his body before the first ribbon of cum shot from his cock, wetting Dean’s hand.

As Sam came, his inner muscles clenched even tighter around Dean’s sensitive cock sheathed inside him and Dean was gone, giving a shout of pleasure as he came inside his brother. Moans of satisfaction spilled from both their throats as they rode out the waves of their pleasure.

Sam almost forgot to roll off Dean when his body collapsed onto the bed, completely sated. Luckily, he moved just in time, landing on the pillow under Dean's head. After all, they were both grown men, so this queen sized bed wasn't exactly big enough for the both of them to be sprawled out on. “That was...wow,” Sam breathed, eyes blinking up at the ceiling. He was in shock – he couldn't believe that they'd just done that.

“Yeah,” Dean answered, nodding as he scooted over a little bit to give Sam more room. “Not a bad reward for losing a game of poker, huh Sammy?” Dean teased, chuckling softly when Sam playfully slapped his chest. “C'mere,” he smiled, pulling Sam against his chest so the younger man didn't fall off the side of the bed.

For a long while, they just lay there, catching their breath after their orgasms. Dean honestly thought Sam had fallen asleep when he nudged him, though the younger man's grunted response let him know Sam was still awake. “Next time we get rooms,” Dean started, leaning in to press a kiss to the top of Sam's head, “we're getting a king.”


End file.
